Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Acetamide and N-Bromosuccinimide

doi:10.1007/s40242-013-2420-4

Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (4): 699-705.doi: 10.1007/s40242-013-2420-4

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Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Acetamide and N-Bromosuccinimide

CHEN Zhan-guo, XIA Wei, WEN Hua, WANG Dan, LI Ya-nan, HU Jun-li

Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, P. R. China

Received:2012-10-31 Revised:2013-02-27 Online:2013-08-01 Published:2013-07-15
Contact: CHEN Zhan-guo E-mail:chzhg@snnu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.20572066, 20906059) and the Natural Science Foundation of Shaanxi Province of China(No.2009JM2011).

Abstract

Abstract:

An efficient method for the one-pot synthesis of 2-oxazolines from ethyl α-cyanocinnamate derivatives with acetamide and N-bromosuccinimide(NBS) in the presence of K₃PO₄ was developed. The reaction was performed smoothly and cleanly to give 2-oxazolines in good to excellent yields(up to 95%) in acetone at room temperature. Thirteen examples were investigated and the results indicated that a large range of α-cyanocinnamate derivatives could be suitable for this method. Based on the outcomes of experiment, a possible consecutive nucleophilic addition-cyclization pathway was proposed.

Key words: One-pot synthesis, Oxazoline, Acetamide, N-Bromosuccinimide(NBS), Regioselectivity, Nucleophilic addition-cyclization

CHEN Zhan-guo, XIA Wei, WEN Hua, WANG Dan, LI Ya-nan, HU Jun-li. Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Acetamide and N-Bromosuccinimide[J]. Chemical Research in Chinese Universities, 2013, 29(4): 699-705.

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Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Acetamide and N-Bromosuccinimide

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